1. Field of the Invention
One aspect of this invention relates to novel vicinal substituted C.sub.4 -C.sub.24 carboxylic acid derivatives, silane and siloxane derivatives thereof, and polymers and copolymers of silane and siloxane derivatives thereof.
2. Description of the Related Art
Organosilicon compounds are extremely useful materials. Simple organosilicon compounds such as alkylsilanes have been used as additives in such things as, paints, hydraulic fluids, heat transfer fluids, and dielectric fluids. Polymeric materials such as polysiloxanes have been used as defoamers, rubbers, coatings, and as additives in emulsions, greases, adhesives, and sealants. Most of these compounds contain silicon-oxygen and silicon-carbon bonds both of which contribute to the many unusual properties of these substances such as strong adhesion to smooth surfaces such as glass, thermal and oxidative stability, chemical these substances such as strong adhesion to smooth surfaces such as glass, thermal and oxidative stability, chemical inertness, resistance to weathering, and good dielectric strength. Because the presence of silicon-oxygen and carbon-silicon bonds contribute to the unique chemical and physical properties of organosilicon compounds, many methods of forming these types of bond have been developed over the years.
In the case of carbon-silicon bonds, one of the most widely used methods of forming them is through the addition of SiH bonds to carbon-carbon multiple bonds. This reaction, which is called hydrosilation or hydrosilylation, is well known in the art and has been used to make many types organsosilicon compounds. The reaction is usually carried out by reacting a substituted silane and a terminal alkene or terminal alkyne. These types of hydrosilylation reactions are normally initiated by heat, light, or radiation and catalyzed by peroxides, bases, and noble metal catalysts. The most widely used catalyst system is one involving chloroplatinic acid or some other platinum complex such as a platinum-olefin complex normally in a single phase system.
The compounds of the present invention can be made by reacting vicinal substituted C.sub.4 -c.sub.24 carboxylic acids and functional derivatives thereof and trisubstituted silanes under standard hydrosilylation conditions similar to those described above. The novel vicinal subsituted C.sub.4 -C.sub.24 carboxylic acids and functional derivatives thereof of this invention contain an OH group vicinal to an ether group whose oxygen atom is bonded to the carbon chain of the carboxylic acid and a linear or branched alkenyl or alkynyl group having from 3 to 10 carbon atoms. Examples of such ether groups include --OCH.sub.2 CH.tbd.CH.sub.2, --OCH.sub.2 CH.tbd.CH, and the like. Compounds similar to the novel vicinal substituted carboxylic acids and functional derivatives thereof of this invention have been described in U.S. Pat. No. 4,315,825. The patent discloses lithium salts of non-terminal vicinal substituted fatty acids having from 16 to 22 carbon atoms wherein the vicinal substituents are a hydroxy group and a group selected from the group consisting of alkoxy having from 2 to 18 carbon atoms, alkenoxy having from 3 to 18 carbon atoms. The patent does not disclose any functional derivatives of these fatty acids such as esters and amides or other metallic salts nor does it suggest that the claimed compounds could be used to make silylated derivatives. Compounds similar to the silane and siloxane derivatives of the novel vicinal substituted carboxylic acids and functional derivatives thereof have been described in U.S. Pat. Nos. 4,659,851 and 4,719,262. These patents disclose organosilicon compounds that contain a plurality of silicon-bonded alkoxy groups and at least one substituent that is bonded to silicon through oxygen a terminal group of the formula CH.sub.2 .tbd.CH--. None of the compounds of the present invention contain a substituent that is bonded to silicon through oxygen that also contains at least four carbon atoms two of which form a terminal group of the formula CH.sub.2 .dbd. CH--. It is an object of the present invention to provide novel carboxylic acid derivatives and hydrosilylated carboxylic acid derivatives useful as coupling agents, emulsifiers and demulsifiers, textile processing aids, and cosmetic additives.